Ammonium Chloride → Methyl 4-([1,1'-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate

HRID 594352

Reaction equation

HRID 594352 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[C:19]([S:23]([N:25]=[CH:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:24])([CH3:22])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([NH:25][S:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:24])[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 750251,1'-Biphenyl, 2-iodo-HCID 86695623Methyl 4-((tert-butylsulfinyl)imino)butanoateHCID 178418339Butyllithium

Product 1

HCID 69082814Methyl 4-([1,1'-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (1.916 g; 6.84 mmol) in anh. THF (62 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (4.27 ml; 6.84 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 4-((tert-butylsulfinyl)imino)butanoate (1.500 g; 6.84 mmol) in anh. THF (8 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 374.12 g/mol.

Workup

  1. stirringstirring
  2. waitwas continued from −78° C. to 0° C. over 1 h
  3. customThe resulting reaction mixture
  4. washThe separated organic layer was then washed with brine (75 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-6db920a20b4347d1a27d0853cf2773bc
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Linked notes

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